Pyropheophorbide A - Compound Card

Pyropheophorbide A

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Pyropheophorbide A

Structure
Zoomed Structure
  • Family: Plantae - Cactaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Chlorophyll Derivative
Canonical Smiles C=Cc1c2[nH]c(c1C)/C=C/1\N=C([C@H]([C@@H]1C)CCC(=O)O)C1=C3N=C(/C=c/4\[nH]/c(=C\2)/c(C)c4CC)C(=C3C(=O)C1)C
InChI InChI=1S/C33H34N4O3/c1-7-19-15(3)23-12-25-17(5)21(9-10-30(39)40)32(36-25)22-11-29(38)31-18(6)26(37-33(22)31)14-28-20(8-2)16(4)24(35-28)13-27(19)34-23/h7,12-14,17,21,34-35H,1,8-11H2,2-6H3,(H,39,40)/t17-,21-/m0/s1
InChIKey RZECWDZMTHMQDD-UWJYYQICSA-N
Formula C33H34N4O3
HBA 4
HBD 3
MW 534.66
Rotatable Bonds 5
TPSA 111.73
LogP 6.95
Number Rings 6
Number Aromatic Rings 3
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 534.26
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Opuntia ficus indica Cactaceae Plantae 371859

Showing of synonyms

  • Bouslama L, Hayashi K, et al. (2011). Potent virucidal effect of pheophorbide a and pyropheophorbide a on enveloped viruses.. Journal of Natural Medicines,2011,65(1),229-233. [View] [PubMed]
Pubchem: 5489042
CPRiL: 59271
Structure

SMILES: O=C1Cc(c2c13)c4nc(CC4)cc5ccc([nH]5)cc6ccc([nH]6)cc(n2)c3

Level: 0

Mol. Weight: 534.66 g/mol

Antiviral

Absorption

Caco-2 (logPapp)
-5.3
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.09
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
1.02

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.84
Plasma Protein Binding
79.18
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.85
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.13
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.04
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.57
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-6783.88
Rat (Acute)
2.96
Rat (Chronic Oral)
3.16
Fathead Minnow
19.88
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
553.15
Hydration Free Energy
-3.08
Log(D) at pH=7.4
3.28
Log(P)
4.91
Log S
-4.57
Log(Vapor Pressure)
-11.06
Melting Point
306.65
pKa Acid
7.8
pKa Basic
5.83
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.9121
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.9121
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8103
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8103
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7928
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7928
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7744
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7744
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7657
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7657
Thymidylate synthase P45352 TYSY_RAT Rattus norvegicus 3 0.7635
Thymidylate synthase P45352 TYSY_RAT Rattus norvegicus 3 0.7635
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7527
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7527
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7522
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7522
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7468
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7468
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7451
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7451
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7410
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7410
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7401
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7401
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7397
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7397
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7349
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7349
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7343
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7343
Phosphodiesterase Q53I60 Q53I60_TRYCR Trypanosoma cruzi 3 0.7342
Phosphodiesterase Q53I60 Q53I60_TRYCR Trypanosoma cruzi 3 0.7342
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7286
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7286
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7266
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7266
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7215
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7215
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7209
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7209
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7203
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7203
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7188
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7188
Genome polyprotein Q99AU2 Q99AU2_9HEPC Hepatitis C virus subtype 1b 4 0.7166
Genome polyprotein Q99AU2 Q99AU2_9HEPC Hepatitis C virus subtype 1b 4 0.7166
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.7160
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.7160
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7131
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7131
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7123
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7123
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 3 0.7017
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 3 0.7017

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